1,8-dimethoxy-(E,Z)-1,7-octadiene | 45037-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,8-dimethoxy-(E,Z)-1,7-octadiene
• 英文别名: 1,8-dimethoxy-1,7-octadiene；1,8-Dimethoxyocta-1,7-diene
• CAS: 45037-90-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: JMTUUFGPZMUWAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  243.0±40.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-dimethoxy-(E,Z)-1,7-octadiene 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 二氯乙基铝 、 一氯化碘 、 四氯化钛 、 烯丙基三甲基硅烷 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (Z,E)-1-trimethylsilyl-trideca-3,9,12-triene-1-yne
  参考文献：
  名称：

  Stereoselective transformation of 1-alkeny ether (R1CH=CHOMe) into alkene (R1CH=CHR2) based on stereospecific elimination of the vicinal iodo(methoxy)alkane

  摘要：

  Treatment of alkenyl methyl ether with ICl rapidly gave 1-chloro-2-iodo-1-methoxyalkane quantitatively. Without isolation, this dihalide was treated with Et3Al to afford anti-iodo(methoxy)alkane in good yield with high stereoselectivity. The stereochemistry of the starting alkenyl ether did not affect the stereochemical outcome of the product. The use of alkynylaluminum ((RC=C)(2)AlEt) resulted in alkynylation of the alpha-chloro-beta-iodoether. Anti-iodo(methoxy)alkane was converted into (Z)-alkene upon treatment with n-BuLi in hexane-ether at -78 degrees C. On the other hand, the reaction of the same anti-iodo(methoxy)alkane with allylsilane-TiCl4 provided (E)-alkene. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01066-7
• 作为产物：
  描述：

  1,6-己二醇 在 草酰氯 、 叔丁基锂 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 1,8-dimethoxy-(E,Z)-1,7-octadiene
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: the use of bis enol ether substrates

  摘要：

  In an effort to develop electrochemical methods for directly initiating oxidative cyclization reactions, the anodic oxidation of bis enol ether substrates has been examined. The reactions were found to lead to the formation of five-, six-, and seven-membered-ring 1,4-dicarbonyl equivalents. The reactions were not found to be useful for generating larger ring sizes. Both alkyl and silyl enol ether substrates were found to be compatible with the conditions required for carbon-carbon bond formation. Cyclic voltammetry studies indicated that the cyclizations were fast and that the reactions happened at or near the electrode surface. Finally, the cyclization reactions were shown to be compatible with the formation of quaternary carbons, even when carbon-carbon bond formation involved the generation of two vicinal quaternary carbons.

  DOI：

  10.1021/ja00029a036